Just a couple of minutes ago I stumbled upon an anime called Kiss x sis. Ignorant as I am I clicked play and what I saw.... wasn't too bad, but at the same time i'm like wtf. One of his "sisters" put chocolate on her lips and told his brother to eat it up.... and eat it up good. Which he did.

it's been quite a while since i saw any of these so not sure which i found to be the oddest, but these four left impression of wtf on me. Bobobo as mentioned before, Excel Saga, Ergo Proxy, and Serial Experiments Lain.
Weirdest recent anime that i actually fully remember because i saw it within last 2 years would be, rin the daughters of mnemosyne.

Just a couple of minutes ago I stumbled upon an anime called Kiss x sis. Ignorant as I am I clicked play and what I saw.... wasn't too bad, but at the same time i'm like wtf. One of his "sisters" put chocolate on her lips and told his brother to eat it up.... and eat it up good. Which he did.

High school delinquent Seiji Sawamura is desperate to have a girlfriend, especially after being rejected by 20 girls as of late. He's afraid that he will end his life with his right hand as his only companion. Apparently, that doesn't change when one day when he wakes up and discovers that his right hand has become a girl named Midori Kasugano, who confesses that she has had a crush on him for the last three years.

I remember thinking "who would watch an anime with such a ridiculous premise?".... then I hit PLAY!

Lol, I like that anime series. One of the very first animes I have ever watched.